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Since Barker, Gupta, and Iantaffi (2007), in both mainstream cultural products and academic literature dealing with BDSM, there has been an increase in emanations of the “healing narrative,” which suggests that BDSM practices offer therapeutic potential. However, no significant attempt has been made to explore in greater detail the problematic relationship between this healing narrative and the history of pathologization of sadomasochistic desires and practices. Barker et al. (2007) rightly point out that in suggesting BDSM has healing potential, one runs the risk of implying that individuals who practice BDSM are in need of healing to begin with. This could be damaging to the image of BDSM, which after centuries of pathologization finally appears to be moving into a realm of acceptability. However, the experiences of BDSM practitioners who describe their practices as healing should not be discounted and could actually help to cultivate a more positive reputation, which makes the issue a political one. In this chapter, through an exploration of the concept of “healing” in cultural objects such as the film Secretary (2002, directed by Steven Shainberg) and the Showtime cable television series Billions (2016–present), this issue will be investigated further, leading to a way out of the apparent double bind. The aim is to come to an understanding of the therapeutic potential of BDSM, which would not only reframe the discourse of pathologization surrounding BDSM but also further the political goal of creating space for BDSM practitioners to explore their desires without having to experience stigmatization.